Malononitrile → Dihydro-2H-pyran-4,4(3H)-dicarbonitrile

HRID 12506

반응식

HRID 12506 반응식
[C:1](#[N:5])[CH2:2][C:3]#[N:4].Br[CH2:7][CH2:8][O:9][CH2:10][CH2:11]Br.CC([O-])(C)C.[K+]>CS(C)=O.CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C(Cl)Cl>[O:9]1[CH2:10][CH2:11][C:2]([C:1]#[N:5])([C:3]#[N:4])[CH2:7][CH2:8]1

참가 물질

7

반응물 3

HCID 8010MalononitrileHCID 21521Bis(2-bromoethyl) etherHCID 23665647Potassium tert-butoxide

생성물 1

HCID 14537194Dihydro-2H-pyran-4,4(3H)-dicarbonitrile수율 24%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

실험 절차

Malononitrile (5.0 g) was dissolved in DMSO (5 mL). Subsequently, bis(2-bromoethyl)ether (9.49 mL) and TBAB (1.22 g) were added, followed by portionwise addition of KOtBu (8.49 g). The mixture was stirred for 4 h. at room temperature, taken up in DCM and extracted 3 times with 5% aqueous NaHCO3. The organic phase was dried over Na2SO4 and evaporated under reduced pressure. The crude material was purified by flash chromatography eluting with PA:Et2O 65:35 (Rf=0.24, visualized with KMnO4) to give 2.49 g (24%) of a solid. 1H NMR (400 MHz, CDCl3) δ 2.24 (t, 4H), 3.87 (t, 4H).

후처리

  1. extractionextracted 3 times with 5% aqueous NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated under reduced pressure
  4. customThe crude material was purified by flash chromatography
  5. washeluting with PA

출처 및 근거

ORD 기록
ord-4052a6dbde5847328dbec77949a0b930
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728018B2

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